6-(4-chlorobutoxy)-4H-1-benzopyran-4-one | 105277-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(4-chlorobutoxy)-4H-1-benzopyran-4-one
• 英文别名: 6-(4-chlorobutoxy)chromen-4-one
• CAS: 105277-72-3
• 化学式: C₁₃H₁₃ClO₃
• 分子量: 252.697
• InChiKey: JHHJLRJRIYICHR-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  405.6±45.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-chlorobutoxy)-4H-1-benzopyran-4-one 生成 6-[4-(4-苯基-1-哌嗪基)丁氧基]-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  JAEN, JUAN C.;WISE, LAWRENCE D.

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 高氯酸 、 水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.75h， 生成 6-(4-chlorobutoxy)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Dopamine autoreceptor agonists as potential antipsychotics. 2. (Aminoalkoxy)-4H-1-benzopyran-4-ones

  摘要：

  The synthesis and pharmacological properties of a novel type of [(arylpiperazinyl)alkoxy]-4H-1-benzopyran-4-ones with dopaminergic activity are described. The nature of the arylpiperazine (AP) moiety determines the dopamine (DA) agonist/antagonist character of this series of compounds; when the aryl portion of the AP is unsubstituted the compounds appear to be DNA autoreceptor agonists while substituted aryl groups seem to impart DA antagonist activity. A heterocyclic piperazine, 7-[3-[4-(2-pyridinyl)-1-piperazinyl]propoxy]-4H-1-benzopyran-4-one (31, PD 119819) has been identified as an extremely selective DA autoreceptor agonist in tests that include [H-3]haloperiodol binding, inhibition of spontaneous locomotor activity, inhibition of brain DA synthesis, inhibition of brain DA neuronal firing, stereotypy assessment, and reversal of 6-hydroxydopamine (6-OHDA) induced akinesia in rats. In addition, 31 possesses good oral activity in the Sidman avoidance test in squirrel monkeys, a predictor of clinical antipsychotic efficacy. In another primate model, 31 has been found to lack the liability for extrapyramidal side effects observed with currently available antipsychotic drugs.

  DOI：

  10.1021/jm00105a039

文献信息

• 4H-1-benzopyran-4-ones and their sulfur containing analogs
  申请人：Warner-Lambert Company

  公开号：US04678787A1

  公开（公告）日：1987-07-07

  Novel 4H-1-benzopyran-4-ones and their sulfur containing analogs are disclosed which are efficacious for the treatment of psychosis including schizophrenia.

  本发明揭示了一种有效治疗精神病，包括精神分裂症的Novel 4H-1-苯并吡喃-4-酮及其含硫类似物。
• Novel 4H-1-benzopyran-4-ones and their sulphur containing analogs
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0190015A1

  公开（公告）日：1986-08-06

  There are disclosed novel 4H -1-benzopyran-4-ones and their sulphur containing analogs which are effecacious for the treatment of psychosis including schizophrenia The compounds have the formula (I) wherein X is oxygen or sulfur, n is 2, 3, 4 or 5 and R is or in which Ar is an aryl.

  已公开的新型 4H -1- 苯并吡喃-4-酮及其含硫类似物可有效治疗包括精神分裂症在内的精神错乱。
• JAEN, JUAN C.;WISE, LAWRENCE D.;HEFFNER, THOMAS G.;PUGSLEY, THOMAS A.;MEL+, J. MED. CHEM., 34,(1991) N, C. 248-256
  作者：JAEN, JUAN C.、WISE, LAWRENCE D.、HEFFNER, THOMAS G.、PUGSLEY, THOMAS A.、MEL+

  DOI：——

  日期：——
• US4678787A
  申请人：——

  公开号：US4678787A

  公开（公告）日：1987-07-07